Process for the production of 8 α, 12-oxido-13,14,15,16-tetranorlabdane

Abstract

The invention relates to a process for producing 8α,12-oxido-13,14,15,16-tetranorlabdane through the cyclizing dehydration of 8α,12 -dihydroxy-13,14,15,16-tetranorlabdane in the presence of aluminophyllosilicates.

We claim: 
     
       1. In a process for the production of 8α,12-oxido-13,14,15,16-tetranorlabdane by dehydration of 8α,12-dihydroxy-13,14,15,16-tetranorlabdane (diol), the improvement wherein said diol is subjected to cyclizing dehydration in a solvent in the presence of a catalyst consisting of at least one alumino layer silicate having an acid charge of from 100 to 300 mval/100 g. 
     
     
       2. The process of claim 1 wherein the at least one alumino layer silicate is present in from about 5 to about 80% by weight, based on the diol. 
     
     
       3. The process of claim 2 wherein from about 15 to about 35% by weight of the silicate is present. 
     
     
       4. The process of claim 1 wherein the cyclizing dehydration is carried out at a temperature in the range of from about 40° to about 70° C. 
     
     
       5. The process of claim 1 wherein the at least one alumino layer silicate has an acid charge of from about 130 to about 180 mval/100 g. 
     
     
       6. The process of claim 1 wherein the at least one alumino layer silicate is acid charged with sulfuric acid. 
     
     
       7. The process of claim 1 wherein the at least one alumino layer silicate is at least one montmorillonite. 
     
     
       8. The process of claim 1 wherein the at least one alumino layer silicate is at least one K catalyst. 
     
     
       9. The process of claim 1 wherein the at least one alumino layer silicate is talcum, a kaolinite, a montmorillonite, a bentonite, and/or a hectorite. 
     
     
       10. The process of claim 1 wherein the cyclizing dehydration is carried out at a temperature in the range of from about 20° to about 110° C. 
     
     
       11. The process of claim 10 wherein said temperature is from about 40° to about 50° C. 
     
     
       12. The process of claim 1 wherein the at least one alumino layer silicate is acid charged with a hydrohalic acid, sulfuric acid, or phosphoric acid. 
     
     
       13. The process of claim 1 wherein the solvent is toluene, xylene, or a mixture thereof. 
     
     
       14. The process of claim 1 wherein the diol is either water-free or contains up to about 2% by weight of water. 
     
     
       15. The process of claim 1 wherein the at least one alumino layer silicate is reused following the cyclizing dehydration reaction. 
     
     
       16. The process of claim 1 wherein water formed during the cyclizing dehydration reaction is removed by azeotropic distillation. 
     
     
       17. In a process for the production of 8α,12-oxido-13,14,15,16-tetranorlabdane by dehydration of 8α,12-dihydroxy-13,14,15,16-tetranorlabdane (diol), the improvement wherein said diol is subjected to cyclizing dehydration at a temperature of from about 40° to about 70° C. in a solvent in the presence of from about 5 to about 80% by weight, based on the diol, of a catalyst consisting of at least one alumino layer silicate having an acid charge of from about 130 to about 180 mval/100 g. 
     
     
       18. The process of claim 17 wherein from about 15 to about 35% by weight of silicate is present; the diol is water-free or contains up to 2% by weight of water; and water formed during the reaction is removed by azeotropic distillation. 
     
     
       19. The process of claim 17 wherein the at least one alumino layer silicate is acid charged with sulfuric acid.